Winter Park FL Property Search

Winter Park FL Homes for Sale

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Available Now in Winter Park - Call Us About These Properties!

$1,495,000
4 Beds 3 Baths Lake Knowles Terrace SubDv. 32789 Zip Code
Nestled in the prestigious "Tree Streets" of Winter Park, this stunning Modern European Cottage-style home exudes elegance and charm. Boasting four generous bedrooms, three full baths, and a spacious second-level bonus room, this pool home combines exquisite design with practical functionality. Enter this welcoming home and feel embraced by the warmth of the wood floors and the exquisite craftsmanship of the base and crown molding, which together create a timeless ambiance that you will love returning to. A formal dining room with a pass-through bar opens to a modern kitchen featuring an extended bar top island, quartz countertops, a Viking Appliance package with a 48' gas range, microwave drawer, and ample cabinet storage. This truly is a chef's dream workspace and an ideal gathering spot for hosting guests. The open-concept floorplan seamlessly flows to the great room with a cozy gas fireplace and tongue-and-groove wood ceiling. The main level primary bedroom is a private sanctuary overlooking the pool with private lanai access and an exceptional luxurious spa bath with dual walk-in closets, a private water closet, and an oversized two-sided walk-in shower. The spacious covered lanai beckons you to relax and unwind by the inviting BEACH ENTRY pool, creating a perfect oasis for both solitude and entertainment. Additional main-level highlights include a guest bedroom, full bath, and laundry room. A rear access stairwell takes you to a versatile 22’ x 14’ bonus room with cathedral ceilings on level two. Two unique bedrooms and a modern full bath can also be found on this level. This home is thoughtfully designed for everyday living, boasting premium finishes throughout. Outside, you'll find a paver drive and covered entry, a 2-car garage, and a fenced yard, offering privacy and convenience. Enjoy the vibrant neighborhood amenities including a park and nearby lakes, while being just minutes away from premier shopping destinations like Park Avenue, Winter Park Village, and Whole Foods. Don't miss the opportunity to experience luxury living at its finest. Schedule your private tour today and make this exquisite Winter Park home your own.

1601 Chestnut Avenue, Winter Park

$549,000
3 Beds 2 Baths Kenilworth Shores Sec 03 SubDv. 32792 Zip Code
Multiple offers. Please submit highest and best offer by Thursday 6/20 at 5:00pm. Experience the charm of Winter Park in this beautifully maintained home, set amidst large oaks in a coveted neighborhood within walking distance to top-rated schools. This inviting residence boasts original hardwood floors and elegant plantation shutters. The lushly landscaped front yard and expansive fenced backyard create a serene outdoor oasis. Entertain with ease on the covered deck and enjoy the sparkling pool surrounded by pavers, perfect for gatherings. The location is unbeatable, with proximity to the hospital, fire station, shops, and restaurants. Inside, the freshly painted home is light and bright, featuring beautiful wood floors throughout the main living areas and bedrooms. The family room and bonus room provide versatile spaces for an office, craft room, or playroom. The interior also includes a spacious family room, a bonus room with indoor laundry, and organized bedroom closets with shelving. The centrally located galley kitchen, equipped with stainless steel appliances and ample storage, offers views of the pool. French doors open to a large covered patio, ideal for outdoor entertaining next to the pool. The expansive fenced yard provides additional outdoor living options. Situated in a neighborhood with a strong school system and convenient access to stores, shopping, restaurants, highways, and parks, this beautiful Winter Park pool home is a must-see. Hurry, it won't last long!

507 Dunraven Drive, Winter Park

$1,929,000
4 Beds 4.5 Baths Northwood Terrace SubDv. 32789 Zip Code
Newer Constructed four bedroom four bath Winter Park pool home is walkable to the East End Market. This Modern styled home has a coastal feel with its straight lines and West Indies touches of wood. Located in the Northwood Terrace neighborhood you experience the best locations of Baldwin Park, Winter Park, and the close market area. A lush Zoysia lawn with tropical landscaping and blooming annuals wow you as you walk up the expansive double drive and entry. An 8 foot French glass door with side lights, adorns the front elevation. Modern sconce lighting as well as additional cedar wood above completes this custom feel. Entering the home, a twelve foot high foyer with inlayed wood and LED lighting completes the entrance. To the right there is a thoughtfully designed first floor guest suite. This suite lends a multi-generational space for guests. Within, another French door offers natural light to the suite. A walk-in shower with beautiful tile/fixtures are just to the right. The grand feel down the hallway continues as double doors roll open to a reveal a large office space. Entering the Great Room there is an incredible 2-story expansive ceiling. This generous room features a 4-panel sliding door, with views to the rear garden/pool and custom landscaping. Adjacent, is the dining area with a modern/bright lighting fixture. A dual panel slider leads out to a covered patio perfect for coffee and breakfast. Back inside, the kitchen is quite the showstopper. Double slab quartz counter tops give a rich feel as does the Thermador Appliance Package. The 48" Freestanding range features six-star burners, as well as a griddle, perfect for quick appetizers or searing your favorite steak or tuna. The 36" Thermador refrigerator offers much space and thoughtful design. An undercounter micro-wave is quiet and out of site. A walk-in pantry has high shelf racks for storage. There is a large glass window behind the sink allowing an abundant amount of sunlight light. As your walk on the opposing side there is a pool 1/2 bath perfect for active kiddos. The primary bedroom is situated behind and features high ceilings with five windows. Hunter Douglas motorized shades are at your beckoning call for complete light out or just filtered light. Another rolling door reveals a luxury treat as you enter the primary bath. Eight-foot glass surround with wall/rain shower heads is just the prescription as is the grand soaking tub. Separate vanities offer private space for each owner to have plenty of room. A custom walk-in closet is in the shape of the letter L and has floor to ceiling shelving for all of your special accoutrements. At the end of the closet is the convenient washer/dryer/laundry room with an ample utility sink. Upstairs there is an open loft/flex space. This area can serve as a play place or exercise area. Two additional bedrooms, each en-suite keeps everyone happy...The backyard private tropical oasis features a 14x32 heated/saltwater pool. A covered lanai as well as the outdoor kitchen makes grilling a snap. Motorized screens on the lanai extend the fun into the evening as there is also a cable hook up for television and entertaining. A whole house generator is included for any power outages. A sought after 3 - Car garage is perfect for the car enthusiast. The home is school zoned for the newly constructed Audubon Park K-8, and the Winter Park School district. This coastal inspired home is available for a private showing. Schedule a visit soon.

2125 Sycamore Drive, Winter Park

$449,000
2 Beds 2 Baths Lake Virginia Condo SubDv. 32789 Zip Code
LAKEFRONT COMPLEX IN THE HEART OF WINTER PARK! This wonderful community is perfectly located on Lake Virgina less than a mile from Park Avenue in Winter Park. Situated on the Fern Canal and seen from the 246 square foot screened in porch with new sliding glass doors. Two bedrooms and updated baths, December 2023-New hardwood floors in the dining room and kitchen, New carpet in the living room and both bedrooms, Interior repainted, linen and a coat closets and an interior laundry with a stackable washer and dryer. The kitchen has Granite Counters, Nice stone backsplash, New Refrigerator, Double oven, Microwave and a large double stainless steele sink. For the dog lovers there is a gated pet area on the canal side of the building. Big bonus is a one bedroom guest suite that can be reserved and rented by the night. Amenities include Lake Access to Lake Virgina, Community Pool, Dock, (Boat Slips available via waiting list HOA Approval) Fitness Center, Ground floor covered parking 1 assigned space, recently updated Recreation room with kitchen, outdoor gas grill, a fire pit, steam and sauna rooms and a storage rack for kayak, canoes or surf board PLUS included is the Water, Trash and City Sewer. Just down the street is Dinky Dock which is a public boat ramp on lake Virginia and access to the entire Chain of Lakes.Walking distance to outstanding restaurants, shoppes, Museums, Central Park, the Sunrail Station and Rollins College.

690 Osceola Avenue Unit 209, Winter Park

$1,490,000
3 Beds 2.5 Baths Osceola Shores Sec 03 SubDv. 32789 Zip Code
Welcome to an incredible opportunity nestled in the heart of Winter Park! One of Winter Park 32789 most desirable neighborhoods - Osceola Shores. Directly across from Lake Osceola and .35 acres. This property presents a prime lot with endless possibilities for renovation or redevelopment. Situated on a spacious 100 x 154 lot, this home offers a coveted split floor plan and an open layout With a bit of creativity and investment, this property could be transformed into your dream home or an exceptional investment opportunity. Detailed remodel building plans may convey with the purchase. The generously sized living room and dining area offer sweeping views of the expansive front and backyard, providing inspiration for indoor-outdoor living and entertaining. The kitchen, updated with newer cabinets and granite countertops in 2015, serves as a focal point with its view of the back porch and pool area. Additional highlights include gas fireplace, original parquet wood floors, utility room, and plenty of closet space. The huge primary suite, with its private access to the pool and ensuite bathroom, offers a large space ripe for customization. Two additional bedrooms share a full bath with vintage tile and bathtub/shower, providing ample space for guests or family members. Beyond the home's potential, the location is unbeatable, with proximity to Park Avenue, Rollins College, The Alfond Inn, Winter Park SunRail station, shopping boutiques, grocery stores, and restaurants. Whether you're looking to remodel and create your ideal home or explore the possibilities of redevelopment, this property offers a rare chance to own a piece of Winter Park's sought-after real estate. Don't miss out on this opportunity – schedule your showing today and bring your vision to life!<div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=EX8qqDvQMeq&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

444 Lakewood Drive, Winter Park

$975,000
3 Beds 3 Baths Hills SubDv. 32789 Zip Code
Prepare to be impressed by this meticulously upgraded Winter Park home, where every detail has been carefully considered to offer the ultimate in comfort and convenience. Beautiful oversized and totally remodeled spit bedroom plan - 3 bed / 3 bath, single-story, brick construction with massive pool, wood-burning fireplace, and entertaining screened porch and patio. All on a private .32 acre lot. Step through the newly installed exterior door handles and locks into a home transformed by a comprehensive renovation. From the garage to the outside pool area, all new electrical wiring ensures safety and reliability. Transformation in 2021 includes - all new ELECTRICAL WIRING, PANELS, tankless gas water heater, chimney flume. Roof replaced in 2017. Added propane gas hookup opens up a world of possibilities, whether it's cooking on the gas oven or envisioning outdoor gatherings around a pizza oven or grill. In 2021- new flooring, interior doors, handles, and custom trim throughout. The laundry room has been thoughtfully expanded - new dryer venting. Brand new AC system, updated ducting, and added insulation for optimal climate control and energy efficiency. Recessed lighting illuminates the main areas. The open kitchen has undergone a stunning remodel, featuring NEW APPLIANCES and custom shelving. Eat-in island, quartz countertops, coffee bar, and designer tile backsplash. Two family rooms plus dining room that can also be used as an office! Bathrooms have been tastefully updated with new toilets and plumbing fixtures. Spacious primary suite overlooks pool area and has lots of closet space. Integrated wifi system including wifi boosters and hard-wired throughout the house for remote workability. Outside, the enhancements continue with new sod and mulch, an electronic wifi-controlled irrigation system, and a dedicated irrigation well for sustainable landscaping. The pool area has been expanded for entertaining. Pool light replaced and Spanish tile on screened-in porch. Perfect for large groups staying out of the sun and tons of dining and conversation area. Outdoor kitchen is ready to go once hooked up to gas. Porch is wonderful for pets too! Additionally, this home boasts a water softener, ensuring the highest quality water for your family. The outdoor patio off the master bedroom is prepped with 3 ft. slab to support future expansion, adding even more value and potential to this already remarkable property. Nestled within a friendly neighborhood on cul-de-sac and positioned atop a hill with excellent schools and a voluntary HOA offering community events, this home offers not just a place to live, but a lifestyle to embrace. Most coveted schools - Dommerich Elementary, Maitland Middle, and Winter Park High School Don't miss the opportunity to make this your forever home – schedule a viewing today!<div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=FKP12jRiFES&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

2421 Mandan Trail, Winter Park

$435,000
4 Beds 2 Baths Eastbrook Sub Unit 11 SubDv. 32792 Zip Code
Location, location, location! Don’t miss out on the opportunity to see this charming 4-bedroom, 2-bathroom home located in this highly sought after Winter Park community. Through the front door you’re brought into the galley kitchen with granite countertops and floor to ceiling cabinetry with plenty of room for storage. This space leads into the formal dining room that circles around to the family room at the heart of the home. Make your way to the back of the home to the instant cabin feel with shiplap ceilings and windows wrapping the entire room for an additional family room off the sliding glass doors. Down the hallway you’ll find the 4 bedrooms with the primary bedroom tucked up at the back. Step outside to the crystal-clear pool in the fully fenced backyard for the ultimate weekend relaxation spot. Solar panels enhance this home that are paid off to enjoy lower monthly bills in these Florida summers! The property is currently rented out with a tenant in place through 11/30/24. With no HOA, this prime location home offers top-rated Seminole County schools nearby and is located near Downtown Orlando and Downtown Winter Park, as well as popular Central Florida theme parks, Winter Park hospital, public golf courses, and near Winter Park's Park Avenue boutique shopping, museums, Rollins College, Full Sail University, YMCA, and University of Central Florida, and so many other modern-day conveniences. Schedule your private showing today!

3463 Arnel Drive, Winter Park

$975,000
3 Beds 3.5 Baths Mondrian/Winder Park Twnhms SubDv. 32789 Zip Code
Introducing a stunning brand-new modern brownstone in the heart of Winter Park, offering access to Lake Killarney. Located in an exclusive community of 30 contemporary townhomes, each meticulously designed residence boasts exquisite finishes, expansive storefront-style windows, and 11' ceilings to flood the interiors with natural light. This 3-bedroom, 3 ½ bath home boasts luxury features that exceed expectations for its price point. A unique layout featuring the main living space on the second level allows you to revel in the seamless flow of the modern kitchen, dining room, and great room. Also located on the second level, a stylish primary bedroom and spa-inspired bath are located in the secluded rear of the home. This retreat includes two walk-in closets, a sitting area, a beautifully appointed bath with designer tile, a frameless glass shower, and a private water closet - thoughtfully designed for your comfort. Additionally, our highly advantageous split bedroom design offers two additional bedroom suites on the first level, providing ample space and flexibility for your lifestyle. With the added convenience of a full-size laundry room, this townhome redefines elegance and functionality. A rooftop oasis complete with an outdoor kitchen, pergola, hot tub spa, and breathtaking views can be found on level three, this thoughtfully crafted space offers the ideal blend of comfort and sophistication. Located in the picturesque Winter Park just north of downtown Orlando, residents can indulge in lakeside living with access to a private boat slip, community kayaks, and a lakefront Pavilion. Whether you seek serene relaxation or vibrant entertainment, this prime location places you moments away from top-tier dining, shopping, and recreational amenities, ensuring a lifestyle of unparalleled convenience and luxury. Additional highlights include the elegant touch of level four drywall throughout, providing a seamless and flawless finish that exudes sophistication in every corner of your home. Illuminate your space with designer-selected lighting fixtures that are sure to make a statement and create the perfect ambiance in every room. Say goodbye to clutter and hello to organization with custom closet systems in every corner, from coat closets to pantries to bedrooms, ensuring maximum storage and style. Walk with grace on Mohawk engineered flooring that offers both durability and beauty, creating a warm and inviting atmosphere throughout your home. Experience the ultimate cooking experience with our Samsung appliance package, featuring a natural gas cooktop and tankless water heater for efficiency and convenience. Embrace luxury with quartz countertops and a stunning waterfall edge island in the kitchen, perfect for cooking, entertaining, and creating unforgettable memories. Step outside to relax and unwind on level three's composite cool decking, a perfect spot for outdoor gatherings and enjoying the fresh air. Park with ease in the oversized two-car garage with an epoxy-painted floor, equipped with a 220V EV outlet for electric vehicles, making it convenient and eco-friendly to power up your ride. Welcome to your dream home, where every detail has been carefully crafted to elevate your lifestyle and offer the perfect blend of comfort, style, and sustainability. Live the life you deserve in our exceptional townhome!

1762 Mondrian Circle, Winter Park

$495,000
3 Beds 2 Baths Casa Aloma SubDv. 32792 Zip Code
Under contract-accepting backup offers. Welcome to 2657 Tierra Circle, a beautifully updated home nestled in a well-established community of Winter Park. This stunning property boasts a perfect blend of modern elegance and timeless charm at an affordable price! Step inside and be greeted by spacious, light-filled living & dining rooms, showcasing freshly painted walls and gorgeous engineered hardwood floors. Anchoring the home is a beautifully remodeled kitchen, complete with granite counters, wood cabinets, and stainless appliances! In addition to 3 spacious bedrooms, this home also features a bonus room/flex space that receives an abundance of natural light… perfect for a home office, game room, or home gym. Step outside to discover a screen-enclosed patio that allows you to enjoy the Florida sunshine year-round, while enjoying the large fenced yard with attractive landscaping! Aside from the aesthetically pleasing updates and improvements that this home offers, you will also benefit from the mechanical and energy-efficient features including WHOLE-HOUSE SOLAR which provides incredible savings in utility bills (average bill is $36!!). Additional updates include a NEW Roof, NEW HVAC system, NEW On-demand Tankless Water Heater, Dual pane/energy-efficient Windows, Custom Plantation Shutters, and updated plumbing and electrical systems! Conveniently located just minutes from Interlachen Country Club, Orlando International Airport, major roads, top-rated schools, shopping, and dining! Enjoy the best of Winter Park living in an affordable home that perfectly balances modern updates with classic charm.

2657 Tierra Cir, Winter Park

$419,000
3 Beds 2 Baths Cedar Ridge Unit 1 SubDv. 32792 Zip Code
Discover the charm and convenience of 1932 Heathwood, a meticulously maintained 4-bedroom, 2.5-bathroom single-story concrete block home located in the heart of Winter Park, FL. This stunning residence seamlessly blends modern updates with timeless appeal, offering an ideal living experience near the vibrant Park Avenue. Enjoy top-tier shopping, dining options, and the highly coveted Seminole County School district. This Winter Park home boasts several recent updates for your peace of mind. Enjoy brand-new impact windows and sliding doors installed in 2022. The HVAC system, replaced in 2020, along with new ductwork in 2022, ensures optimal year-round comfort. A fresh exterior paint job from 2019 enhances the home's curb appeal. The master bathroom features a contemporary walk-in shower installed in 2022. In 2023, additional insulation was added, boosting energy efficiency and home comfort. The spacious, oversized 2-car garage provides ample room for vehicles and storage. The large fenced backyard is a private retreat complete with a storage/utility shed, perfect for all your outdoor needs. This Winter Park home is a blank canvas, ready for its new owners to add the finishing touches and make it their own. With all major updates already completed, you can focus on personalization and style. Don't miss this exceptional opportunity to own a slice of Winter Park paradise. Schedule your private showing today and experience the perfect blend of modern living and prime location at 1932 Heathwood.

1932 Heathwood Drive, Winter Park

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